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CHEBI:8673 - pyrimethamine

ChEBI IDCHEBI:8673
ChEBI Namepyrimethamine
Stars
DefinitionAn aminopyrimidine that is pyrimidine-2,4-diamine which is substituted at position 5 by a p-chlorophenyl group and at position 6 by an ethyl group. It is a folic acid antagonist used as an antimalarial or with a sulfonamide to treat toxoplasmosis.
Last Modified19 June 2017
DownloadsMolfile
FormulaC12H13ClN4
Net Charge0
Average Mass248.717
Monoisotopic Mass248.08287
SMILESCCc1nc(N)nc(N)c1-c1ccc(Cl)cc1
InChIInChI=1S/C12H13ClN4/c1-2-9-10(11(14)17-12(15)16-9)7-3-5-8(13)6-4-7/h3-6H,2H2,1H3,(H4,14,15,16,17)
InChIKeyWKSAUQYGYAYLPV-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
antiprotozoal drug  Any antimicrobial drug which is used to treat or prevent protozoal infections.
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
EC 1.5.1.3 (dihydrofolate reductase) inhibitor  An EC 1.5.1.* (oxidoreductase acting on donor CH-NH group, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of dihydrofolate reductase (EC 1.5.1.3).
Applications:
antiprotozoal drug  Any antimicrobial drug which is used to treat or prevent protozoal infections.
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
ChEBI Ontology
Outgoing Relation(s)
pyrimethamine (CHEBI:8673) has role antimalarial (CHEBI:38068)
pyrimethamine (CHEBI:8673) has role antiprotozoal drug (CHEBI:35820)
pyrimethamine (CHEBI:8673) has role EC 1.5.1.3 (dihydrofolate reductase) inhibitor (CHEBI:50683)
pyrimethamine (CHEBI:8673) is a aminopyrimidine (CHEBI:38338)
pyrimethamine (CHEBI:8673) is a monochlorobenzenes (CHEBI:83403)
IUPAC Name 
5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine
INNs  Source
pyrimethamineChemIDplus
pirimetaminaChemIDplus
pyrimethaminumChemIDplus
pyriméthamineWHO MedNet
Synonyms  Source
2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidineChemIDplus
2,4-Diamino-5-(p-chlorophenyl)-6-ethylpyrimidineChemIDplus
2,4-Diamino-5-chlorophenyl-6-ethylpyrimidineChemIDplus
5-(4'-Chlorophenyl)-2,4-diamino-6-ethylpyrimidineChemIDplus
5-(4-Chlorophenyl)-6-ethyl-2,4-diaminopyrimidineChemIDplus
5-(4-Chlorophenyl)-6-ethyl-2,4-pyrimidinediamineChemIDplus
Manual XrefsDatabases
C07391KEGG COMPOUND
D00488KEGG DRUG
DB00205DrugBank
PyrimethamineWikipedia
HMDB0014350HMDB
CP6PDBeChem
LSM-3967LINCS
1912VSDB
Registry NumbersSources
Reaxys:219864Reaxys
CAS:58-14-0KEGG COMPOUND
CAS:58-14-0ChemIDplus
CAS:58-14-0NIST Chemistry WebBook
Citations